


Try, Try Again

by youaresunlight



Category: Supernatural
Genre: 5+1 Things, Alternate Universe - College/University, Fluff, M/M, Misunderstandings, Mutual Pining, Professor Castiel, Professor Dean
Language: English
Status: Completed
Published: 2015-08-25
Updated: 2015-08-25
Packaged: 2018-04-17 06:47:13
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,135
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4656744
Author URL: https://archiveofourown.org/users/youaresunlight/pseuds/youaresunlight
Summary: <blockquote class="userstuff">
              <p>Five times Dean asks out fellow professor Castiel Novak, and one time he gets it right.</p>
            </blockquote>





	Try, Try Again

The first time Dean asks out Castiel Novak, he does so with a pair of tickets in his hand and a tongue that refuses to pronounce any French.

“It’s a foreign film festival,” he explains, his mouth drying up at the sight of Cas who tilts his head and regards him curiously. “They’re also showing some older movies that were popular and, uh... _Un Long Dimanche_? Sammy recommended that one. I mean, not that I don’t watch French movies myself.”

Cas’ mouth quirks up in a smile and it’s such a soft gesture, quiet but sweet. “It was very kind of you invite me, Dean,” he says, but his expression falters and so does Dean’s courage, “and I wish I could go but it’s my sister’s birthday that weekend. I’ll be out of town until Sunday night.”

The ‘I’m sorry’ is written all over Cas’ face and Dean knows he’s being earnest; Cas is too good a guy to feed him a lie. So, he replies, “That’s okay. We can do something else another time.” His heart skips at Cas’ visible relief and he takes the tickets back home to give to Sam and Jess.

 

◇ ◇ ◇

 

The second time Dean asks him out is in the middle of a condiments aisle at a Trader Joe’s. He’s eyeing a jar of caramel sauce in half-guilt, all-interest when a voice behind him calls out his name. “Dean?”

Dean turns around and nearly drops his basket on the floor. “Hey, Cas.”

He has never seen Cas out of his work clothes, ever - carefully pressed slacks and button-up shirts and sometimes a tie he can’t get to lie properly. But right now, Cas is wearing slightly torn jeans and a flannel shirt, a plaid of blue criss-crossing with grey that makes his eyes look absolutely incredible.

“You know, apples go well with that caramel sauce,” Cas smiles. Dean’s only reply is to blush and laugh, and manage a “Thanks, that’s good to know.”

His eyes then drop to Cas’ basket where boxes of teas fill up half the space, a medley of jasmine and green and orange blossom and he blurts without pause, “Would you like to get tea with me sometime?”

“Tea?” Cas asks helplessly, and Dean just wants to _run_ straight into the jams.

“Sorry, uh, guess that doesn’t make much sense.” Dean waves a hand toward Cas’ groceries. “You’ve already got, you know, so I’ll just... See you tomorrow, Cas.”

It’s a _complete_ disaster.

 

◇ ◇ ◇

 

The third time comes sooner than expected, as Dean leaves a faculty meeting for the English department. He thinks he might pull his hair out if Zach says ‘synergy’ one more time, but the line of thought quickly dissipates once he sees Cas round the corner in his glasses.

“Department meeting?” Castiel asks. He furrows his brows and it’s absurdly adorable. “Did Zachariah mention synergy again?”

The question makes Dean laugh, open and genuine, because regardless of his crush, he and Cas are friends. “Not a real meeting if he doesn’t,” he teases, and when Cas crinkles his nose in amusement, it takes everything for Dean to not pull him into his arms. “So, what brings you to this side of our building? Did the French department get too French for you?”

Castiel huffs. “I teach twentieth-century French literature, Dean. It is literally my job to be too French.” His eyes are fond and Dean’s heart is racing. “I came to use the copier since Balth claimed ours. He’s copying exams for all three of his sections.”

“Oh, right, well knock yourself out.” Dean clears his throat and cocks his head toward the supply room before he adds, “Hey, by the way, I’m staying behind to grade some papers, so if you’ve also got work, maybe after we could-”

And then Cas’ phone starts to ring.

Cas peeks at the screen and looks up apologetically, “I have to take this. What were you saying about...?”

Dean inwardly groans but smiles all the same. “Nah, it’s nothing important. You should answer that.”

 

◇ ◇ ◇

 

The fourth time is much like the first time, and he has a table for two booked at the Italian place on Third. Benny suggested it the minute Dean started to mope about his hideous crush, and he’s feeling somewhat hopeful as he walks to the office pods, passing Balthazar along the way.

“Cassie’s inside,” he smirks all knowingly. Dean flushes but grunts and ignores it.

“Hi, Dean,” Cas greets brightly when Dean shows up in his doorway. He’s at his computer, glasses perched on his nose, sporting a tie smattered with bees that should be cheesy but really isn’t. “What’s going on?”

“Heya, Cas,” Dean leans on the doorframe. He glances at the floor then up at Cas again. “Do you have any plans for Friday night?”

Cas pauses, appearing to mull it over. “No, I don’t believe I do yet.”

Relief washes over him; he’s halfway there. “How do you feel about going to dinner with me? I wasn’t sure if you like Italian but I heard...”

“I do like Italian,” Cas cuts in gently, “despite my teaching focus.”

Dean grins. “So, how ‘bout seven?”

Cas ducks his head. “Seven sounds great, Dean,” and it’s truly the best thing Dean has ever heard.

He’s essentially on cloud nine throughout the week, close to pinching himself because it all seems too good to be true. So, of course, when Thursday night comes around, the world has to remind him that he can’t be so lucky.

“I’m so sorry,” Cas croaks over the phone, sounding miserable and tired and sad. “I was looking forward to our dinner very much.”

“Hey, it’s alright,” Dean sighs, more out of concern than anything else. “Just take care of yourself, okay?” He hopes that his tone conveys he means it.

Cas’ nose is a bit red when he makes it to campus the next day; the silver lining is that he has just one class to teach, a seminar in the early afternoon. His voice is still a little hoarse, lower and rougher than usual, and he apologizes to Dean once more, which reminds Dean that he needs to call and cancel the reservation.

 

◇ ◇ ◇

 

The fifth time is over before Dean even has a chance to say anything. It’s almost a month later and he’s about to ask if Cas wants to try for dinner again, but then there’s a guy in Cas’ office, all dark hair and hazel-green eyes.

Dean has no idea who he is - definitely not a professor from any department Dean’s familiar with. None of that matters when the guy reaches up to ruffle Cas’ hair, a show of clear affection that makes Castiel smile and roll his eyes.

So, Dean turns and walks away before either notices his presence. Not that they would while being so caught up in each other. Frustrated, Dean scrubs a hand over his face and heads back to work to dive into his grading.

 

◇ ◇ ◇

 

The sixth time is sort of an accident, since Dean has realized that Cas is now taken. He hasn’t brought up movies or tea or dinner or any of that, and if Cas has noticed anything, he doesn’t say so as Dean tries his best to get over him.

“What are your plans for the weekend?” Cas asks. He’s checking his mail while Dean uses the copier (Charlie currently has control of the one in the English department).

“Uh, well...” Dean presses Start and lets the machine run. “Sam’s been bugging me to check out the farmer’s market, so I might do that to get him off my back.”

Cas smiles softly. “Is this the one they have at the park?”

Dean nods. “Yeah. We should go together, Cas.”

The words are out before he can stop them, and he freezes as the silence passes. _What the hell_ , _Dean_ , he scolds himself, the self-berating switching to surprise when Cas says, “I would love to, Dean. When should I meet you?”

“What?” he replies, so totally eloquent, but Cas is still smiling and it’s unfairly pretty. “Oh, I... You actually want to?”

“Yes,” Cas says slowly, squinting a little and looking vaguely hurt. “Unless... If you don’t- I wouldn’t want to...”

Dean has to stop him. “No, I’m sorry. That came out wrong. How’s noon? The thing goes till four.”

The smile is back. “Noon will work great.”

 

◇ ◇ ◇

 

Dean figures, especially given the handsome mystery man in Cas’ office, that Cas intends the outing to be a hangout between two friends. And Dean is okay with that, although deep down he wishes it were more, and so at eleven am on Saturday, he has to tell himself _not_ to dress for a date.

The last thing he wants is for Cas to be uncomfortable, to receive any more hints of Dean’s suppressed feelings. So, he bypasses the limited number of date-worthy shirts he does own and goes for a print tee and semi-nice jeans instead.

“Let’s try not to be too obvious, Dean,” he mutters, though he can’t help himself from smoothing his palms over his shirt.

Cas is nearby a baker’s stand when Dean finds him in the middle of the crowd, catching Dean off guard with how nicely he’s dressed - in a pale blue shirt and dark grey pants. “Hi, Dean,” he offers a smile, his hair mussed from the breeze coming through, and Dean finds it difficult to speak for a bit because Cas is so wonderful yet completely out of reach.

“Hey, Cas,” he finally says. “You look nice. Did you have something earlier?”

Cas appears slightly confused, until something seems to dawn on him and his cheeks color pink. “N-no, I...” His lashes flutter nervously. “I just thought-” He stops short to stare at the ground.

“Cas,” Dean takes a step closer. He wants to reach for Cas’ hand but somehow manages to restrain himself. “What’s wrong? Oh, god, I put my foot in my mouth again, didn’t I. You know, I tend to do that, which probably isn’t great since I _teach_ and everything. I just get so... You’re really... Christ, I’m rambling now.”

“No, I apologize. I misunderstood,” Cas says. He’s still subdued but looks up at least, although Dean is confused by _what_ he misunderstood. “I thought- When you asked me to accompany you, I thought...” He lets out a shaky breath. “I’d assumed this was a date.”

It takes Dean a moment to work out what he says.

“You did?”

Cas drops his eyes, his bottom lip all red from him biting it. “You asked me to the film, a-and dinner and... Please know that I _wanted_ to do all those things.”

“Cas...”

“Everything just kept refusing to cooperate with me and I realize it must have been frustrating for you. And when you didn’t mention it for a while, I thought you might’ve moved on, which is more than understandable.”

_I could never_ , Dean wants to say, but Cas keeps talking, blushing and frantic.

“But then we spoke yesterday and I was so relieved. I came here hoping to ask you to lunch, or... or dinner at that restaurant we didn’t make it to before. Of course, I’m happy to just stay without _any_ of that if you’re no longer interested. I could also go; I don’t wish to make you uncomfortable and-”

“ _Cas_.”

“... Yes?”

Dean shakes his head and closes the distance between them, hands coming up to cradle Cas’ face and maybe he’s laughing too because they’re such idiots.

“Cas,” he repeats, softer this time, and he doesn’t think he’ll ever tire of saying that name.

“Yes, Dean?” Cas replies. He sounds breathless, looks so hopeful, and Dean’s heart might burst at his expression alone.

“Will you go around this farmer’s market with me? And yeah, as a date. As in, I’d like to hold your hand?”

Cas’ lips part and his baby blues are huge now, so beautiful. “Yes,” he murmurs back, and Dean grins so widely that his cheeks actually hurt.

“Then, later, could I take you to dinner?”

Cas lifts a hand and curls it warmly around Dean’s wrist. “Yes.”

“And, ah... tea? Maybe tomorrow?”

Castiel laughs. “Yes, absolutely.”

“Good, and there’s the movie too.”

“You don’t mind the subtitles?” Cas teases lightly.

“I’m an English professor,” Dean winks playfully. “I like reading English,” and he kisses the corner of Cas’ mouth.

 

◇ ◇ ◇

 

As it turns out, the guy Dean was worried about is Castiel’s brother, Michael Novak. “He’s the oldest and I’m the baby of the family,” Cas laughs, a few dates later when they’re lounging on Dean’s couch, pressed close. “I can’t believe you were jealous of him, Dean,” he hums, smiling into their next kiss at the feel of Dean’s fingers running tenderly through his hair.

**Author's Note:**

> [Rebloggable link here](http://puppycastiel.tumblr.com/post/127590495625/deancas-try-try-again)
> 
> Do leave me your comments and those little heart things if you're so inclined!
> 
> [Tumblr](http://puppycastiel.tumblr.com) | [Twitter](http://twitter.com/leeshwrites)


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